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104 Properties Available In Winchester
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- Price-High To Low
- Price-Low To High
- Newest Listings
- Beds (Most)
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$3,989,000
Single Family Home
26 Swan Road, Winchester, MA 01890
Nestled in the heart of Myopia Hill, this custom-built home is sure to impress! Live your best life at 26 Swan Road offe...
Listed by Kim Covino & Co. Team of Compass
$2,398,000
Single Family Home
74 Hillcrest Parkway, Winchester, MA 01890
Introducing 74 Hillcrest Parkway! This spacious, modern 5-bedroom home is nestled across the breathtaking Middlesex Fell...
Listed by Ann Charlotte Hogstadius of RE/MAX Real Estate Center
$3,250
Condo
115 Washington Street #2B, Winchester, MA 01890
Stunning unit in the heart of Winchester with easy access to Boston and the surroundings. Conveniently located near com...
Listed by Vijoy Abraham of Abraham Realty
$975,000
Single Family Home
18 Pine Grove Park, Winchester, MA 01890
Beautifully maintained one owner Cape, ideally located near Winchester Center. Nestled on a neighborhood street, with Ho...
Listed by Michele Forester of EXIT Premier Real Estate
$1,299,000
Condo
261 Cambridge St #261, Winchester, MA 01890
Step into this beautifully renovated historic townhouse that seamlessly blends classic charm with modern updates. This w...
Listed by Katie Tully of Better Homes and Gardens Real Estate - The Shanahan Group
$4,799,000
Single Family Home
19 Rangeley Rd, Winchester, MA 01890
A treasure. That's how this residence is viewed, throughout town, throughout the decades. One family had the vision to b...
Listed by The Pallotta Group of Advisors Living - Winchester
$2,999,000
Single Family Home
8 Chestnut St, Winchester, MA 01890
Newly constructed 5,366 sq ft luxury home with attached 2 car garage! Featuring 5 bedrooms, 4 full and 2 half bath, and ...
Listed by The McLaren Team of Compass
$869,900
Single Family Home
79 Sylvester Ave, Winchester, MA 01890
Discover where form meets function in this beautifully maintained home, ideally located near Winchester Center. Nestled ...
Listed by Anne Spry of Barrett Sotheby's International Realty
$2,399,000
Single Family Home
88 Arlington Street, Winchester, MA 01890
Welcome to this warm & inviting home nestled amidst the serene landscapes of the Winchester Country Club. A Royal Barry ...
Listed by Kim Covino & Co. Team of Compass
$3,199,000
Single Family Home
12 Prospect St, Winchester, MA 01890
Exuding elegant luxury, this fully renovated Victorian boasts a carriage house and extraordinary grounds, in one of Winc...
Listed by The Pallotta Group of Advisors Living - Winchester
$4,500
Single Family Home
17 Russell Rd, Winchester, MA 01890
Single-family home with 3 bedrooms and 1.5 baths. Move in date: 6/1/2025. Tenant pays all utilities (gas, heat, electric...
Listed by Tsz Mui Kwan of Kwan Realty Inc.
$699,900
Condo
7 Conant Rd #20, Winchester, MA 01890
Beautifully renovated first-floor condo in the highly sought-after "Willows at Winchester" complex. This expansive, sing...
Listed by Brian Woods of Woods Properties Inc.
$1,899,000
Single Family Home
4 Olde Lyme Rd, Winchester, MA 01890
This stunning 4-bedroom, 4-bath modern home offers the perfect blend of luxury and tranquility. Featuring soaring vaulte...
Listed by The Pallotta Group of Advisors Living - Winchester
$3,699,000
Single Family Home
54 Johnson Road, Winchester, MA 01890
This newly constructed home faces Old Village Dr. & redefines modern luxury! Designed w/ both elegance & everyday comfor...
Listed by Kim Covino & Co. Team of Compass
$2,899,000
Single Family Home
5 Clearwater Rd, Winchester, MA 01890
Welcome to a rare opportunity to select the final finishes in your dream home right within Winchester's most coveted nei...
Listed by The Marrocco Group of Coldwell Banker Realty - Lexington
$3,450,000
Single Family Home
58 Wedgemere Ave, Winchester, MA 01890
Experience the timeless charm of this stunning English Tudor in Winchester's coveted Flats neighborhood. Set on an overs...
Listed by Mark Donnellan of Advisors Living - Winchester
$4,200,000
Single Family Home
3 Foxcroft Road, Winchester, MA 01890
Nearing completion! Welcome to this exquisite 6-bedroom, 5-1/2 bath residence nestled in one of Winchesters most prestig...
Listed by Kim Covino & Co. Team of Compass
$3,599,000
Single Family Home
2 Chestnut St, Winchester, MA 01890
Welcome to 2 Chestnut Street, an exquisite new construction home in progress by Mark Stephen Development. Situated off c...
Listed by Mark Donnellan of Advisors Living - Winchester
$1,599,000
Single Family Home
189 Mystic Valley Pkwy, Winchester, MA 01890
Great price improvement - Ready to go at this price! Nestled in the heart of downtown Winchester, the stunning Barstow H...
Listed by Anne Spry of Barrett Sotheby's International Realty
$2,200
Condo
200 Swanton St #428, Winchester, MA 01890
Bright and sunny 1 bedroom and 1 bathroom condo in Winchester Park View. close to shopping, restaurants, town Center and...
Listed by Wei Wang of WW Real Estate LLC
$4,199,000
Single Family Home
6 Vinson Cir, Winchester, MA 01890
Nestled on a cul-de-sac in Winchester's desirable west side, this brand-new construction redefines modern luxury living....
Listed by Peter Kasseris of Coldwell Banker Realty - Lexington
$11,000
Single Family Home
52 North Border Rd., Winchester, MA 01890
Grand and masterfully crafted home on this private road abutting 2200 acre Fells conservation land. This spacious home h...
Listed by Julia Marino of Archambault Real Estate
$2,649,000
Single Family Home
3 Lagrange St, Winchester, MA 01890
Nestled in a sought-after neighborhood, this stunningly reimagined home combines timeless charm and modern comfort, just...
Listed by Mark Donnellan of Advisors Living - Winchester
$5,000
Single Family Home
27 Ledyard Road #SF, Winchester, MA 01890
SHORT TERM RENTAL - Oversized cape with hardwood floors throughout. Large front to back living room with working fire...
Listed by Diane Plunkett of Plunkett Properties